A long few years ago, after Brittany and I split ways, I was in a hard spot and couldn't seem to get out of this funk. SOO, in an attempt to move forward with myself and my life, my buddy Austin invited his girlfriend Sabra (Now Baby momma) and her Friend Skyler over to spend the night. We set up shop in the basement where we had a couch, against the back wall, a recliner a few feet from the couch, a few sleeping bags, some blankets, also, and entire, HUGE open room with a pool table along with all of the laundry room stuff, and some other things my mom had set out for arts and crafts and such.
I was kind of skeptical of the idea at first, I wasn't too sure about having Sabra over, we didn't see eye to eye on anything, and she DEFINITELY was a shady little psychopath. There was a smidge of drinking, but nothing intense. I got acquainted with Skyler pretty easily, she wasn't the prettiest thing, but she was available. It didn't take long for us to get close, we clicked and laid back with one another. Austin hopped up and suggested a quick smoke down so, we all stepped outside, and smoked a little pinner (joint) and came back downstairs after grabbing a few refreshments from the kitchen. Austin and Sabra cozied up in the recliner, didn't last too long though, neither of them could get comfortable at all. Me and Skyler took the couch. Of course we all had discussed the nature of this visit, and were all fine with the "Hook up for the night and see how it works out" plan.
Skyler wasn't wearing a whole lot to begin with when they showed up, pretty simple get up really. Pair of jeans, slightly tattered, and an old black band t-shirt. Her hair was done up in a ponytail, but didn't stay that way. Sabra was a little more sluted up, but essentially had the same get up. When it came time to settle in however, that changed up pretty quickly. Skyler and Sabra stepped off into the upstairs bathroom, meanwhile Austin and I were basically just hanging out in the basement waiting around. He gloated about how he "TOLD ME" this was a great idea and how maybe if I finally got laid, things would turn around. I brushed it off as we watched the 2 girls start down the stairs. Sabra was wearing some booty short pajama bottoms and a white tank top, Skyler walked down in nothing but a REALLY long faded white T-shirt and some underwear under it.
I was kicked back on the couch, Austin was laid out in the recliner. Just as swiftly as I realized that they were walking up behind us, is just as fast as I saw Skyler's leg swoop over my body and her plop down on my lap. Sabra made a smart ass remark and, we all laughed and laid back. It wasn't long before Austin and Sabra ended up on the floor under the blankets. It also wasn't long before it was realized that Austin was having some issues. Sabra got to complaining about his performance, or lack of, and me and Skyler are just busting out laughing the whole time. Sabra AND Austin snapped up about us "distracting them", NOBODY could help but bust out laughing at that point. We re-focused though, and Skyler and I started playing around with one another.
So I'm laying back on the couch, with Skyler on top of me, Austin and Sabra are trying desperately to get ANYWHERE on the other side of the room, and so we begin.
Looking deeply into Skylers eyes, I can see all of the hurt, all of the repression she just wants to rid herself of. I get it, and with a soft touch, I lifted up her shirt, and ran my hands up her sides and across her stomach. I reached up and firmly squeezed on her breasts, she really didn't have ANY kind of tits..like a B cup at best, but a mouthful is all that was needed in that time. She did however, have a fantastic ASS. Oh My God that ass! It wasn't perfectly rounded, bubbled out, or whatever the mainstream industries try to convey to be what the "Perfect Booty" is; It was natural, and it had a lot of meat on it that I couldn't get enough of. She was a little plump, not like obese, but she had some baby fat left on her, right where it needed to be. Her love handles were perfect in that sense, and I had the best leverage to put them to use. She sat on my lap, kind of grinding me, but not getting to heavily into it. It was enough to get my dick hard and for her to feel and size out what it was going to be like to fuck. When I was fully erect is when she started giving me looks, I slipped my shirt off over my head and tossed it to the side, hearing Austin bitch about how I needed to stay on my side of the room. Couldn't help but laugh at him and Sabra, continuing to listen to them struggle it out cause, he couldn't keep it up, and she was just loosing interest in it all together.
Me and Skyler kind of made out for a few, stopping to laugh at Austin and Sabra who were just having a SERIOUS problem on the other side of the room; They eventually gave up all together and decided they were going to go to sleep. In the meantime, me and Skyler got super close in a very sexy way. Her moans got a little more intense as she would grind on my hard cock, we would have to re-situate every so often cause my dick would get caught up and try to slip in her ass. Not that I was opposed to it, but it kid of hurt when my dick would bend up without any kind of warning. She had slipped off her underwear and hopped right back up on top of me, I pulled my dick out, and slid my boxer briefs onto the floor, again, Austin and Sabra popped up bitching about "Staying on our side of the room". Again with a good laugh in the moment, Austin and Sabra decided to go out for a smoke instead of sitting downstairs with me and Skyler; She still had her shirt on so we both were covered up where we would have needed it. With her grinding her pussy on my dick, splitting her lips with every thrust, I grabbed her ass, gave it a good squeeze and lifted her up onto my hard cock. Her moans got louder as I would lift her up off me and let her slam back down. Looking up at her face while this was going on made it worth the while in keeping her hairy pussy unacknowledged. She squatted herself lifted up off the couch while I held onto her love handles and beat on her pussy, slapping my balls off her underside then, pulling her down onto me as relaxed back on the couch. I was smacking her ass while she ground herself so deeply on my dick, and we heard the door upstairs open. Austin and Sabra were on their way back down stairs, so we cooled it for a moment, they got themselves situated back under the covers and tried to get something started again. Sabra got a little piece but, it didn't workout for them in the end. She got super pissy and rolled over to go to sleep. Austin sighed, and followed her in the roll. Me and Skyler started up again, and just as fast as the first moan started, was about as quick as Sabra perked up and decided to kick us out of the room because she wasn't getting any dick, so why the fuck should anyone else be happy right?
I took Skyler into the other room, we walked slowly over to the pool table. There was a carpet square surrounding the table, as we locked eyes, I put my hands on her shoulders and brought her to her knees. Grabbing her hair as she wrapped her hand around the base of my shaft, she opened her mouth as wide as she could; Stuffing my dick in her mouth, but it didn't fit too well. I wrapped my hands around the back of her neck and face fucked her for a few moments. Her Jaw started to lock up so I let go and let her go at her own pace. She wrapped both hands around my fully erect, bulging cock; Twisting her hands and her head around the base and tip. Jerking my dick while she bobs down on my cock, I'd grab on the back of her head and hold her down, forcing my dick as deep as it would go down her throat without her gag reflex getting overworked. I'd let her come back up for air and then she's right back at it. Pulling her hair up like it were in a ponytail, while she wrapped her hands around my hips, I went back to face fucking her. I could tell her Jaw was completely worn out when her teeth started scraping against my dick, she pulled off and asked if we could take a break. I obliged and we stood up.
As we stood back up, I turned her around, and smacked her ass, leading her to the Pool Table. Bending her over the side of the table, I grabbed my dick by the base and rubbed it between her lips. With a little tease I found the gap I was looking for and, SLAMMED my dick in her pussy. Spanking her as while I did so, holding onto her love handle with my left hand, and grabbing a handful of ass in the other, I gave her a good smack and gripped the other hand tightly around her waist. Her moans got louder and more intense, I grabbed her by the mouth trying to muffle the sound but, it was no use. I pulled out of the position we were in, throwing her leg up onto the edge of the table. I spread her ass and dove back in, throwing hard hands while I beat the shit out of her from behind. A few spankings later, I let off the love handles, pulled her off the table, turning her around to grip her up by the ass and sit her back down on the edge. Throwing her legs up over my shoulders, I reached for her tits, playing her nipples like little violins while I rammed my dick back in her pussy. Occasionally I would reach back down and rub out her clit while I was still pounding her, she would come back and do the same. Her face would constantly change, from her wide eyed and kind of shocked, to closed eyes, biting her lips tilting off to the side, to mouth wide open but no sound or breaths coming out, letting out subtle squeaks and harder moans. I put her legs down and grabbed her by the waist, slamming back into her as hard as I could. She would breathe out in a very low tone, "FASTER, HARDER, MORE MORE MORE". All I could come back with was a more intense thrust that eventually got me knocking my thighs off the edge of the table.
I slowed myself and backed off the table, grabbing Skyler up by her wrists and turning her toward the support beam that was right behind me. As expected she bent over, grabbed on the pole and spread her legs apart. I grabbed my dick up and flicked it between her lips again, she hopped up on her tippy toes and we were off. I caught the gap and dropped my dick in her nice and hard. She immediately grabbed hold of her mouth, holding back screams of pleasure while I gripped her ass cheek, gave it a good smack, and preceded to break her ass open against the pole. I got tired of standing though, so I dropped her down to doggy style. Her legs are kind of longer than mine so it only really worked with me kneeling and hitting her kind of sideways from the back. My dick would be pressured, bending against the wall of her vagina. Her moans got a little quieter, so I stood up and crouched above her ass, moving myself up, I dropped my cock deeper inside as I would sit down on Skylers ass, holding her love handles while I did so. Eventually that got tiring though, so we switched back and forth between that and me beating her ass in doggy style.
Hours had past at this point, and I still hadn't even come close to cumming. I stepped up and off, spun her around so we were face to face and asked her if she would try anal. She sketchily said she would give it a try so, I spat on the tip of my dick, and massaged her asshole with it. Pulling away to try and moisten her asshole with a good glob of spit, I rubbed the rim and got a finger in to try and loosen the edges, I brought my dick back in play and got the tip in. Swirling my cock around trying to get an in into her tight little asshole, it was no good though. She pushed back on my abdomen and asked me if I'd be mad if she wanted to NOT do anal. I said no, and turned her back to the pole. Not before I had her drop to her knees and blow me again though. She wrapped her hand around the base and I threw my dick down her throat like the crumbs on the bottom of your favorite bag of chips. We were sweating so hard you couldn't see the distinction between her cum, and both of our sweat covering the floor. Spanking her ass while I continued to pound her ass from behind; I basically just started throwing her around like a rag doll. From the floor, back to the table, from behind. Opening her legs on the carpet by the Pool Table, on the edge of the Pool Table...The Pool Table was used a lot that night, never once for a game of pool.
I was tired, dehydrated, and wanted a cigarette in an EXTREME type of way. We had been going at it for what was found out to be going on 8 hours straight, NON-STOP, switching positions and going in all over again. I pulled out while she was clinging onto the pole for dear life, and taking a look at my dick, I had never seen it so big. It was red, throbbing, thicker AND longer than I had ever recognized. I was ready to call it.
Turning Skyler back to the pole, I went in as hard as I could, as fast as I could go. Gripping on her ass, Throwing good hand prints on it with every few thrusts. I busted out every bot of force I had in me in these lasts moments of our very long night. I started feeling the build up, more and more pressure began to build up inside of me. Finally, I turned Skyler back on towards me, dropped her to her knees, and shoved my dick in her mouth. I told her this is how were gonna end it but, obviously she didn't have much of a choice in the matter. Grabbing her by the back of the neck and face fucking her until....BOOM, the largest load I probably ever nutted is now down her throat. Gagging every squirt that got let go, she never once backed off my cock. Of course, I did kind of have her pinned down anyway but, all in the same, when she got her gags under control, she grabbed onto and started jerking my dick while sucking out whatever remained in the shaft of my massively erect dick.
Finally being able to take a break here, we got ourselves covered up. Skyler threw her shirt back on, and I put on my boxers. As we stepped out for a cigarette, Austin and Sabra perked up and started joking on about how loud and long that ride was. We all stepped out on the porch, me and Skyler wrapped up in a blanket, sitting on the steps inside the porch. It was light outside by the time we had finished our rounds in the basement, we had decided to watch what was left of the sun rise before we went back downstairs. While we were out, Sabra had come up with the Nickname "Pool Table" for Skyler. It fit pretty well, and stuck for a good long while. As the session came to an end, me and Skyler went to lay down for a while BUT, Austin and Sabra wouldn't SHUT THE FUCK UP cause, apparently they didn't get any sleep that night on the count of me and Skyler..So our punishment was being kept awake by the 2 fucks who actually slept cause, BOTH of them were salty as fuck over things not working out between them. Fuck it though, can't be mad about the amazing night that was prior to all the bullshit.
Our lives went on and, we kind of kept touch, but not really. Today, if I didn't have respect for women from what I have learned in the past, and how much I've experienced in the wrong sense...I would probably do unspeakable things to Skyler...well I guess not unspeakable in this case...but I would probably make sure anal entered the picture this time around. So Anyway, I hope you've been entertained, I have plenty more stories so please, keep reading. Both of erotic and just funny kind of fucked up tales of myself and being On My Way.
Written and lived by: Zachery Lee
This is part of a series. Check out the main series of "On My Way" over on Families here!